Top 15 Books Read in Five Years in Chicago

15. Zen and the Art of Motorcycle Maintenance: An Inquiry Into Values by Robert Pirsig

The only work of “fiction” cracks the list at number fifteen. I put fiction in quotes at its really a philosophical textbook intermingled with a novel about a father and son cross-country roadtrip. It’s worth noting that the author just passed away a few months ago. The New York Times obituary and retro-review of the book do it justice, and concludes with the epilogue Pirsig himself wrote for the novel:

“There is a Swedish word, kulturbärer, which can be translated as “culture-bearer” but still doesn’t mean much. It’s not a concept that has much American use, although it should have….

Culture-bearing books challenge cultural value assumptions and often do so at a time when the culture is changing in favor of their challenge. The books are not necessarily of high quality. Uncle Tom’s Cabin was no literary masterpiece but it was a culture-bearing book. It came at a time when the entire culture was about to reject slavery. People seized upon it as a portrayal of their own new values and it became an overwhelming success….

This book offers another, more serious alternative to material success. It’s not so much an alternative as an expansion of the meaning of “success” to something larger than just getting a good job and staying out of trouble. And also something larger than mere freedom. It gives a positive goal to work toward that does not confine. That is the main reason for the book’s success, I think. The whole culture happened to be looking for exactly what this book has to offer. That is the sense in which it is a culture-bearer.”

14. Bubble Logic: Or How I Learned to Stop Worrying and Learned to Love the Bull by Cliff Asness

I was hesitant to even review this because it’s a long paper (about 50 pages), and wasn’t published as a book. But it’s length just passes my threshold, and it’s such an important read that I had to share it. The author is a billionaire investor only occasionally recognized outside the financial industry. This paper, written at the height of the 1990s dot-com bubble, served as not only an accurate predictor of the bubble-burst, but a precise one. Asness’s mathematical takedown of bubble logic is swiftly and decisively deconstructs human’s poor decision making abilities. Given what we have seen in the past year in the cryptocurrency markets and in the mid-2000s real estate bubble, it’s as relevant as ever.

13. The Black Swan: The Impact of the Highly Improbable by Nassim Taleb

Taleb is a bit of a cult hero these days, and this book is what started it. While I was in college (2008-2012), this book (published in 2007) became a sensation in the financial community for its ability to not only predict the financial crisis, but provide a mathematical and philosophical framework (informed from the author’s own experience in the financial industry in the 1980s) for understanding its causes and consequences. While not everyone likes his writing style, his messages are too important to be ignored.

12. The Management Myth: Debunking Modern Business Philosophy by Matthew Stewart

This two-part tale shines a bright light on the dangerous, long-held myths about “business management”. A former management consultant recounts his own time in the industry (both at top name-brand firms and spin-off independents) and researches the history of “management theory” starting from the industrial revolution. What he finds is obvious to those least empowered to change these practices: most of traditional consulting industry theory is either outdated or was never accurate to begin with, are filled with scientism, and the real answers are much closer to social science and philosophy than business school. It’s a fantastic insider expose on an industry which exists to capitalize on people’s weaknesses inside large organizations.

11. Fooling Some of the People All of the Time: A Long Short Story by David Einhorn

Often, doing the right thing is hard. It’s even harder when “the establishment” is completely against you. David Einhorn, professional investor and unintended detective, writes his memoir of his hunt to take down corrupt and shady business loan provider Allied Capital. It covers all my favorite topics in a non-fiction story: An underdog raging against the machine, simple explanations of complex financial industry minutiae, and a detective story of real-world big business corruption. I thank David for documenting his service to society.

10. Zero to One: Notes on Startups or How to Build the Future by Peter Thiel and Blake Masters

In a brief 100-or-less pages, venture capitalist Peter Thiel and his protege succinctly convey Peter Thiel’s worldview. The books’ title has become a tech startup cliche shorthand for bringing new innovation to the world. This ranks so highly in my list as I don’t think I’ve read a book with a higher value-per-word ratio than this, so I’d recommend everyone take an evening or two to complete it.

9. Indecent Exposure: A True Story of Hollywood and Wall Street by David McClintick

When I recently reviewed another book, I wrote: “My favorite genre is probably “business epics”, a category label I just made up to cover longform biographies done of companies. The historical leaders of this genre (and some of my all-time favorite books) are Barbarians at the Gate, Indecent Exposure, and The Smartest Guys in the Room.”

Indecent Exposure is the oldest of the group and served as an inspiration for many business journalists who followed in McClintick’s footsteps. It’s the “All the President’s Men” of business dramas. It’s not short, but the true absurdity gripped me all the way through this masterpiece on the greed and egos running high-profile industries.

8. What Do You Care What Other People Think?: Further Adventures of a Curious Character by Richard Feynman

I had already read the classic “Surely You’re Joking, Mr. Feynman” in college. This spiritual sequel is a collection of fewer essays, but contains a couple of much greater emotional and intellectual impact. Specifically, there are two must-read tales: First, Feynman’s reminiscing on the last year of his wife’s life leaves an impression for its emotional honesty. Second, and the largest chunk of the book, is his now-infamous Challenger story, where Feynman uncovers and explains to the government why the space shuttle exploded after launching. These two stories, emotional and intellectual, paint a fuller picture of one of the greatest minds humanity has seen.

7. Diary of a Very Bad Year: Confessions of an Anonymous Hedge Fund Manager by Keith Gessen and n+1

Possibly the best book written on the 2008 financial crisis. Keith Gessen, a fantastic writer at n+1 magazine, serves as the everyman while interviewing a friend-of-a-friend who happens to be a professional investor during the Great Recession. Each chapter is a new interview occurring about every three months, spanning a two year period. Over the course of time, The Anonymous Hedge Fund manager educates Gessen (and by proxy, the reader) on the high-level philosophy of financial industry, and the brutality of the day-to-day workings on an industry in disarray. The concept (collecting these interviews over a long period during tumultuous times) is brilliant and the execution is flawless.

6. Antifragile: Things that Gain from Disorder by Nassim Taleb

“Wind extinguishes a candle and energizes fire.” So begins Taleb’s magnum opus (although he does have a new book coming out in 2018, so he may disagree with that description). Where his prior books highlighted problems, Antifragile moves closer to prescribing, or at least describing, solutions. I prefer not to try and summarize nuanced ideas into a one-liner. This book is for anyone who wishes to be more like fire and less like a candle (or more broadly be able to adapt and thrive in an uncertain world).

5. High Output Management by Andy Grove

As I did in my 2016 review, I’ll just repeat Ben Horowitz’s quote on this book and the amazing man behind it:

Andy himself was a legendary figure. He had grown up Jewish in Hungary during a time when the country was occupied by the Nazis and, later, by the Soviet Communists. Arriving in New York, he spoke no English and had almost no money. He enrolled himself at the City College of New York, overcame his language deficiency, and went on to get a PhD from UC Berkeley. This nonnative English speaker would then write an important textbook on semiconductors in English while working at Fairchild Semiconductor. As a result, he was considered a scientific pioneer even before helping to launch Intel in 1968, building it into the seminal technology company of the era. Later, in 1997, Time magazine would recognize his nearly impossible accomplishments and name him Man of the Year. This is in part what made High Output Management so extraordinary. Andy Grove, who built himself from nothing to run Intel, stopped what he was doing to teach us his magic. And not through some ghostwriter either — Andy wrote this book himself. What an incredible gift.

4. Born Standing Up: A Comic’s Life by Steve Martin

The best biography I’ve read since college. Much like Dave Chappelle in the early 2000s, Steve Martin stepped down from the standup comedy industry while he was still at the top of the field. But that’s not the noteworthy part. What Steve Martin conveys is the struggle required to reach greatness. The years of performing in front of empty rooms, working odd jobs to make ends meet, and grinding toward an unknown future. It’s told in a compact, straightforward style that is accessible to anyone. If you read it, just maybe it will inspire you to leave all your blood, sweat, and tears on your metaphorical field of dreams.

3. Enough: True Measures of Money, Business, and Life by John Bogle

As the founder of the sensational money management firm Vanguard, Bogle has a unique vantage point on how the financial industry is designed to stealthily steal money from the rest of society. In this concise, consumable manifesto, Bogle lays out important principles for improving our financial industries, corporate America, and our personal lives.

2. But What If We’re Wrong? Thinking About the Present As If It Were the Past by Chuck Klosterman

When I previously described Klosterman as a “cultural philosopher”, I meant that not only were the topics about pop culture, but Klosterman writes in a uniquely intelligent way that’s palatable for anyone (the closest comparison to this style I can think of is the scripts from Frasier and The Twilight Zone). The ideas discussed in “But What If We’re Wrong” are simultaneously thought-provoking, relatable, profound, and accessible.

1. Command and Control: Nuclear Weapons, the Damascus Accident, and the Illusion of Safety by Eric Schlosser

The “Illusion of Safety”, as Schlosser subtitles it, is such a profound point that it can’t be understated. As I alluded to in my review of this book, there is essentially no grander story that can be told than the true story of how humanity could have created its own nuclear apocalypse, and the slim margin of error by which we’ve avoided it thus far

This review is kept short because there aren’t enough bits in our collective computers to capture all the superlatives I’d use to describe it. I rarely find a new book that both breaks into my personal pantheon of favorites and is something that I’d recommend to everyone.

“An entire generation has been raised without experiencing the dread and anxiety of the Cold War, a conflict that lasted almost half a century and threatened to annihilate mankind. This book assumes that most of its readers know little about nuclear weapons, their inner workings, or the strategic thinking that justifies their use. I hope readers who are familiar with these subjects will nevertheless learn a new thing or two here. My own ignorance, I now realize, was profound. No great monument has been built to honor those who served during the Cold War, who risked their lives and sometimes lost them in the name of freedom. It was ordinary men and women, not just diplomats and statesmen, who helped avert a nuclear holocaust. Their courage and their sacrifices should be remembered.”